#1 Clearwater Jazz Holiday
The Clearwater Jazz Holiday returns to Coachman Park this weekend, October 16-19th, with an all-star lineup including Trombone Shorty, Cory Wong, and Trampled by Turtles. Enjoy 4 days of world-class jazz, funk & blues along Clearwater’s waterfront. Learn more at https://www.paradisenewsfl.com/clearwater-jazz-2025/.
#2 Gulfport Night Market
Stroll, shop, and soak up the vibes at the Gulfport Night Market, happening again this Saturday 5-9pm. Held year-round on the first Friday and third Saturday each month, the market brings together local makers, artisans, and food vendors under the management of Tampa Bay Markets, now celebrating 15 years of successful events. Presented in partnership with the Gulfport Merchants Chamber, it’s the perfect evening for community fun, unique finds, and coastal charm. Bonus events this weekend include release for the book “Gulfport Rising” at DRV Gallery 5:30-8:30pm, Gulfport Rising Benefit Concert at North End Taphouse 12-10pm & Artist Meet & Greet with Sue Johnson at Brenda McMahon Gallery 6-8pm.
Learn more at https://www.tampabaymarkets.com/gulfport-night-market.
#3 St. Pete Pier Fall Festival and Drone Show
Celebrate autumn this Saturday, October 18th 11am-9pm at the St. Pete Fall Fest on the St. Pete Pier! This free community event transforms the waterfront into an autumn wonderland, complete with a pumpkin patch, fall-themed photo ops, and festive décor perfect for capturing those seasonal memories. Stay for the rescheduled 727 Day Drone Show- a breathtaking spectacle as over 1,000 synchronized drones light up the night sky to tell the incredible story of the City of St. Petersburg. Free admission!
Learn more at https://stpetepier.org/event/st-pete-fall-festival-2/.
#4 Vaughn Pickleball Tournament
Get ready to rally for a reason at the Vaughn Law Pickleball Invitational this Saturday, October 18th at Skybeach Resort in St. Pete. This event is more than just a tournament – it’s a community-powered day of fun. With multiple divisions (Men’s, Women’s, & Mixed Doubles), local sponsors, awesome swag, and a post-match Celebration Social Hour, this is your chance to play hard & give back even harder. Proceeds support Give Joy Collective’s Christmas for Fosters.
Learn more at https://www.paradisenewsfl.com/vaughn-law-pickleball-invitational/.
#5 SPO presents Susannah
Head out to The Palladium in St. Pete this weekend for St. Pete Opera’s production of Susannah. A young girl blossoms into beauty in a small town in rural Tennessee. Her only relative is her drunken brother, her only friend the son of disapproving church leaders. The male church elders come upon Susannah bathing nude in a creek by her house. Instead of seeing innocence, they project their own sins upon the girl. One wicked act breeds another in this tale of intolerance, betrayal & loss.$15-$130.
Get tickets at https://stpeteopera.org/event/susannah/.